Abstract
[Reaction: see text] C-Phenyl-N-erythrosylnitrone 3 behaves as a C1,C1' bis-electrophile, undergoing a double addition of Grignard reagents in a domino fashion to afford acyclic hydroxylamines 4. The reaction proceeds at 0 degrees C with variable degrees of diastereoselectivity, from moderate to good, mainly depending on the organomagnesium reagent used. The usefulness of compounds 4 has been exemplified with the synthesis of pyrroloazepine 12 through a ring closing metathesis key step.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Anions
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Aza Compounds / chemical synthesis*
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Aza Compounds / chemistry
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Carbon / chemistry*
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Glycosylation
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Heterocyclic Compounds / chemical synthesis*
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Heterocyclic Compounds / chemistry
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Magnesium / chemistry*
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Molecular Structure
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Nitrogen Oxides / chemistry*
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Organometallic Compounds / chemistry
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Stereoisomerism
Substances
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Anions
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Aza Compounds
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Heterocyclic Compounds
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Nitrogen Oxides
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Organometallic Compounds
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nitrones
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Carbon
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Magnesium